At age 15, Green started performing stand-up comedy at local clubs, most notably at Yuk Yuk's comedy club, and went on to do this for two and a half years until he canceled a booking to go to New York for his rap group.[3][4][5]

While attending Algonquin College as a member of the Sigma Pi Fraternity, Green hosted an overnight call-in show on the University of Ottawa's campus radio station, CHUO. The 1990 show, originally a rap music show entitled The Rap Show, was followed by an electronic music show hosted by Glenn Humplik. Through the proximity of their shows, Tom and Glenn met and became friends, based on a common love of zany antics. Tom's radio show soon shifted formats to a call-in show (upon the discovery of how to operate the studio's call-in lines)[citation needed] and the two joined forces to host The Midnight Caller Show (which lasted from 1993 to 1996). The basic format of The Midnight Caller was to have listeners call-in with Tom and Glenn making fun of them (or "razzing" them) and soon after hanging-up on them. The show's novelty and originality made it an underground hit[citation needed] in the Ottawa area.

In 1998, Not The Green Tom Show was released by Green's alter-ego MC Face. The theme of the album revolves around MC Face, a pugnacious and foul-mouthed rapper who is constantly angry with and taking verbal jabs at Tom Green, his square producer who brings on some of his buddies from The Tom Green Show.

Green soon had his own non-paid television show on public-access television on cable TV. The first incarnation of The Tom Green Show aired from September 1994 until 1996 as a one-hour no commercial public cable access program on Rogers Television 22 in the Ottawa region airing 50 episodes in two seasons.[6]The Tom Green Show was a variety show format, where he would have guests visit the studio and bands play before a live audience. He also had taped segments that typically consisted of stunts played by Green on unsuspecting people. A number of them involved Green's parents, Richard and Mary Jane, who consistently appeared unamused and occasionally angered by Tom's antics. In October 1996, The Tom Green Show aired one time as a pilot on CBC. The show was later picked up in Canada by The Comedy Network in 1997 and aired 26 episodes over the course of two seasons.[6]

The Tom Green Show was then picked up by MTV in January 1999, where he gained popularity in the United States and worldwide. The format of the MTV version of the show was similar to his original show; it was hosted by Green and co-hosted by two of his long-time friends, Glenn Humplik, who occupied the couch, and Phil Giroux, who sat behind a window at the back of the set and became known as "the guy in the window" usually drinking cups of coffee. Derek Harvie, who co-wrote the show with Green, occasionally appeared in the segments. Many of the sketches were targeted at his parents, both of whom appear to be unimpressed and embarrassed by their son's antics.

The Tom Green Show was renowned for Green's version of shock humor. Some of Green's most notable skits include pretending to "hump" a dead moose (which was referenced by rapper Eminem in "The Real Slim Shady"), having an X-rated lesbian scene painted on his father's car (labeled the "Slut Mobile"), drinking milk by sucking on a cow's teat, and putting a cow head in his parents' bed while they slept because his father was a fan of The Godfather films. Green also hung his own unauthorized piece of art in the National Gallery of Canada (which remained untouched for days) with the added twist of later coming back and vandalizing it to the horror of onlooking patrons.[7]

In a segment, Green went to the press conference of Grey Owl where he serenaded and kissed Pierce Brosnan. Brosnan, thinking Green was a journalist, advised him not to give up his day job. Green also did many segments humiliating his co-host and longtime friend Glenn Humplik; even after the pair had become well-known, Humplik continued working at his phone company job, fearing that his entertainment career might not last. Green teased him about this often and once gave out Humplik's office phone number on the air.

Green eventually wrote a song called "Lonely Swedish (The Bum Bum Song)", which he composed during MTV's Spring Break while doing a show on a cruise ship. After airing the music video on his show and appealing to his audience to request it, the song became an instant number one hit on Total Request Live and was also referred to in Eminem's song "The Real Slim Shady". He quickly called for the video to be retired because "it's not fair to 98 Degrees." Later, in his autobiography, he revealed that MTV had pressured him to do so in order to maintain the image that Total Request Live was, in fact, a live request show (the next week's episodes had been pre-taped on location, and the producers of the show were completely unaware of "The Bum Bum Song" at the time).

Green's increasing fame made it harder for him to ambush people during man-on-the-street segments, leading him to target mostly senior citizens and non-English speakers. After he was diagnosed with testicular cancer in March 2000, he stopped production on his TV show, but he continued to appear on the channel via reruns and other promotional materials. Green's popularity during this time led to him gracing the cover of the June 8, 2000 issue of Rolling Stone magazine.

The MTV show Jackass debuted six months after The Tom Green Show went on hiatus. Many of the segments on the show had close similarities to the segments from Green's show: Bam Margera rudely awakening his parents, the cast of Jackass falling down while on crutches, swimming with sharks, etc.[8]

In early 2000, Tom Green was diagnosed with, and successfully treated for testicular cancer.[9] Green wrote, directed and starred in a one-hour MTV television special entitled The Tom Green Cancer Special (aired on May 23, 2000[10]) which documented the time leading up to his surgery and included graphic footage of his own surgery. The episode received wide critical acclaim for revealing a vulnerable, human side of an otherwise juvenile television personality.[11] During this time, he started the "Tom Green's Nuts Cancer Fund" to raise money for cancer research.[12] In mid-2000, Green also spoke in front of thousands of students in the University of Florida and sang a song entitled "Feel Your Balls" to help educate others about testicular cancer.[13]

Although it was Green's cancer that caused The Tom Green Show to cease production, a frequent rumor says that the show was cancelled because of an alleged segment where Green shows up at a bar mitzvah, or another Jewish event, dressed as Adolf Hitler. Green, however, has repeatedly denied that such a segment exists, and there is no evidence to suggest that such an event occurred.[14] He mentions the rumor in his 2004 autobiography, Hollywood Causes Cancer, stating that it apparently started when some Boston teenagers were caught videotaping themselves performing a similar stunt and when asked by security, they used the name "Tom Green." Green says, "I would never do a mean-spirited, anti-Semitic joke like that - it's both abhorrent and not funny. To this day I still get asked about it, and it's annoying. So again, for the record, it didn't happen. There is nobody on this planet that has ever seen this bit on tape because it does not exist. If it did exist, it would have certainly reared its ugly, hateful head on the Internet by now. But it won't, because it doesn't exist. I've never put on a Hitler costume. In fact, I've never even been to a Bar Mitzvah."

Freddy Got Fingered won in five categories at the 2001 Golden Raspberry Awards, given to the worst movies of the year. Green appeared at the ceremony to accept his awards, making him the first performer to do so in the award's twenty-year history, and the second recipient to do so following director Paul Verhoeven for Showgirls in 1995.[15] Green arrived at the awards ceremony in a white Cadillac, wearing a tuxedo and rolled out his own red carpet.[15] After accepting the awards, Green stated "When we set out to make this film we wanted to win a Razzie, so this is a dream come true for me".[15] While onstage, he began to play the harmonica and did not stop until he was dragged off.

In July 2000, Tom Green became engaged to actress Drew Barrymore. Green and Barrymore met after Barrymore, who was a fan of Green's show, asked Green to appear in Charlie's Angels, which Barrymore starred in and produced. Green and Barrymore married on July 7, 2001.[16] In Green's book Hollywood Causes Cancer, he writes "We [Drew and Tom] lived together for a year before we were engaged, and we were engaged for a year before we got married".[17] Barrymore also appeared in her then-fiance's infamous 2001 film Freddy Got Fingered.

During the buildup to their wedding Green and Barrymore frequently joked with the media about when and where they were going to wed. The most notable incident came on November 18, 2000, when Green hosted the American television show Saturday Night Live. During the monologue, Green brought Barrymore on stage and teased the audience about the couple marrying at the end of the episode. Ultimately, the stage was set for a wedding before Barrymore, in the end, got "cold feet" and left Green alone to end the show. The SNL incident initially left viewers and the media confused about whether the couple had actually planned to marry on live TV, or were simply staging a publicity stunt. Eventually, Green also went on The Tonight Show with Jay Leno to toy with the public once again, this time claiming that his bride might be pregnant.[citation needed]

On February 18, 2001, there was a house fire at the residence shared by Green and Barrymore. Their dog Flossie woke them around 3:30 a.m. when she barked and "literally banged on their bedroom door." Firefighters estimated damage at $700,000 in the two-story, 3,500 square foot (325 m2) home located north of Beverly Hills at 9500 Cherokee Lane. The incident was soon spoofed on Saturday Night Live with guest host Katie Holmes playing Drew Barrymore and Jimmy Fallon playing Tom Green.[18] On October 13, 2001, Barrymore hosted Saturday Night Live and Tom Green appeared in the audience wearing a gas mask.

In 2002, Green starred in and directed a one-hour MTV special called The Tom Green Subway Monkey Hour, where he tormented strangers in Japan. During 2002, Green also started his own production company called Bob Green Films;[20] he starred in and was executive producer for a half-hour special entitled The Skateboard Show on The WB.[21]

In mid-2003, after Green guest-hosted The Late Show with David Letterman, MTV gave him his own late-night talk show called The New Tom Green Show. The critically acclaimed show lasted several months and the show consisted of a traditional monologue, segments, followed by interviews with guests. Green in numerous interviews has stated that David Letterman was one of his early influences.[6]

A notable incident included Jesse James Dupree, the frontman of the Southern rock band Jackyl, when he made the ill-advised decision to take a chainsaw to Green's new desk on the show. The unplanned stunt clearly irritated Green and he made no attempt to hide his displeasure. He eventually began his planned musical performance (himself on drums and Dupree on guitar) but continued to verbally spar with Dupree for a short period before abandoning the drums mid-song in apparent disgust and walking off stage. Later on in the evening, he again insulted the band by holding up Jackyl's most recent album and advising viewers to "check it out if you like music that was cool fifteen years ago" and then proceeded to smash it with a hammer.

In September 2003, the show was cancelled by MTV eleven weeks after its premiere due to low ratings.[22] Reports indicate that ratings and viewers for the show averaged 889,000 viewers in the first week and then averaged 255,000 viewers in the last week for the reruns.[23] In Green's book Hollywood Causes Cancer, he stated that the show, "was very expensive to produce and not really the type of show that MTV has been traditionally known for."[24]

On October 12, 2004, Green released his autobiography[25]Hollywood Causes Cancer: The Tom Green Story which discussed in detail his Hollywood career, short-lived marriage to Drew Barrymore, and his experience dealing with testicular cancer.

A notable incident discussed in the book involved Green on character-based talk show Primetime Glick with Jiminy Glick (played by Martin Short).[25] Green wrote that this un-aired interview was the first time he walked off any show, and this was due in part to Short being "mean" and making fun of his testicle.[26] When Short brought up the incident in a 2005 interview, Green defended his stance on his online blog.[27]

In 2005, Green returned to rap and started the group, The Keepin' it Real Crew, featuring DJ EZ Mike of the Dust Brothers, where they did two Canadian live tours (June 2005 and January 2006).[28] On December 6, 2005, Green released his second solo album in Canada entitled Prepare For Impact, which included a bonus DVD featuring footage from his live tour. The album was also co-produced by Mike Simpson of the Dust Brothers. The album included comedic tracks (such as "My Bum Is On Ya Lips" and "I'm an Idiot")[28] as well as serious tracks where he rapped about his Hollywood career.

In March 2009, on Last Call with Carson Daly, Tom played a sample of his new song "It's Been A Long Time Coming." On his website, Green has stated intentions of releasing a new rap album in 2010 and talks about working with music producer Detail. In a February 2010 interview, Green mentioned an upcoming song entitled "Other Side Of The World" and stated that he was developing a television show following the progress of his first major American rap album.[4] On a November 2010 answer to a fan question in the Forum section of tomgreen.com, Green said, "Expect some singles in the future. The album is dead, sadly."

In July 2011, Green recorded and posted a 2011 remix of "Check The O.R." and re-united Organized Rhyme at the Just For Laughs festival in Montreal. In October 2011, The Comedy Network's website posted the group's new music video: "Check The O.R. Redux".

In the 2000s, Green has tried to put some of his more controversial material behind him and become a more mainstream entertainer. During the Leno era of The Tonight Show, Green was a recurring contributor to The Tonight Show with Jay Leno; he has done many segments where he travels across America looking for "interesting people", typically bringing the most colourful person with him back to the studio. In these segments, the focus is more on the odd behavior of the interviewees, with Green generally playing the straight man.

In 2003, Green visited troops in Kosovo on a USO tour. He visited troops in the Persian Gulf on a 2004 tour.[20] In early 2006, Green appeared in several commercials for the Canadian Cable Public Affairs Channel promoting both The Channel and encouraging voters to participate in the forthcoming federal elections, which took place on January 23, 2006.

On August 3, 2006, Green appeared on America's Got Talent. He rode a skateboard through a flaming hoop, appeared to be on fire for a few seconds, and was put out with extinguishers. It was confirmed on the August 3 episode of Tom Green Live that it was a stunt man, not Green, that did the stunt.

Green has made several appearances as a celebrity contestant on the ABC reality game show Wanna Bet?, including the show's premiere episode in July 2008. He was also a contestant on the 2009 season of The Celebrity Apprentice.[31] Throughout the season, each celebrity raised money for a charity of their choice; Green selected the "Butch Walts and Donald Skinner Urologic Cancer Research Foundation."[32] He was fired by Donald Trump on the third episode, while acting as project manager, primarily due to waking up late on the day of the task - he had been out drinking with Dennis Rodman the night before. On August 4, 2009, Green made an appearance on the American version of Hell's Kitchen as a celebrity guest diner. In late 2009 and early 2010, he appeared on the first two seasons of For the Love of Ray J to judge the contestants on the show. On that show, Green has been credited for coining the popular catchphrase, "She smashed the homie."[4]

In 2005, he starred in a children's TV movie, Bob the Butler, and made guest appearances on various kid's shows. Since then, Green has been starring in low-profile independent films such as the 2008 movies Shred and Freezer Burn: The Invasion of Laxdale, and the 2009 movie Shred 2.

In February 2010, Green announced that he had finished editing an independent film titled Prankstar, which he also starred in, wrote and directed.[35] On a November 2010 answer to a fan question in the Forum section of tomgreen.com, Green stated that the film was going to be released soon as he had "just made a deal with a big time distributor so it's gonna be cool."[citation needed]

Green was on the March 21, 2013 episode of Workaholics and the March 25, 2013 episode of Canadian television series Seed. He was also in the 2014 Trailer Park Boys 3: Don't Legalize It movie. Green has also made many appearances on the Canadian revival of the game show, Match Game.

Since launching his web show in 2006, Green has conducted long-format interviews with hundreds of guests; and has since then, taken various podcasting projects and re-launched his live show on television in 2013 using the same interview format. In an October 2013 interview, Green stated that he preferred "great interviewers who know when to sit back and listen" rather than being an interviewer that "wanted to be as funny as the guest and...get into a sort of competitive relationship with them".[36]

On June 5, 2006, ManiaTV.com announced they had formed a partnership with Green to host a live talk show from his own living room in the Hollywood Hills overlooking the San Fernando Valley. The first show aired live on June 15, 2006 at 11 pm EST, was originally called Tom Green Live!, and was airing Mondays through Thursdays.[37] In January 2008, shortly after Green's split from ManiaTV, the show was renamed Tom Green's House Tonight. The shows are broadcast live at TomGreen.com. A pared-down version was later broadcast on The Comedy Network and various local channels in the United States, until Green stopped syndicating the show to television. On a 2009 blog, Green noted that he stopped his show from syndication on television due to dissatisfaction with his lack of creative control. He continues to broadcast the show from his website. Green later started a monthly subscription service that allowed subscribers to have full access to all the videos on his website.

Due to lack of an established term, Green often refers to his live streaming broadcast as "Web-o-Vision." He also jokingly says he is broadcasting to "The National Internet", despite the show having a worldwide audience. Green often refers to his show as, "The highest rated, longest running, and only talk show on the Internet."

From Green's website, Tom Green's House Tonight typically aired live on weeknights at 10 pm EST, although shows can begin at any time during the day and night. The shows were then archived on his website. The format of the show often includes Green taking live telephone calls and Skype video calls where viewers around the world are able to chat with Green and his guests. Green would often be a victim of prank calls due to the live nature of the show and would sometimes voice his frustration with the callers. On top of the live web show, Green has added many video segments from his past as well as present.

In 2007, "Tom Green Live" won the 2007 TV Guide "Online Video Award" for Best Web Talk Show. In 2008, Tom Green's House Tonight won a 2007 Webby Award for "Best Variety Show".[38]

When Green does not have guests, he has done many unconventional shows such as playing the saxophone for an hour, having a week dedicated to performing karaoke, or updating the viewers about The Channel while taking telephone and Skype calls.

On his website, Green has talked about the substantial costs of continuing the online show and that The Channel may be gone in mid-2011 if it is not profitable by then. In 2011, Green ended the subscription service on his website and stated that his live show is on hiatus. Green also took down the TV studio that was in his living room.

From October - December 2010, Green did seven weekly podcasts interviewing guests at Kevin Smith's SModcastle. This was done in a long format interview style in a theater that held an audience of 50 people.

On September 25, 2013, it was announced that Green will be hosting a new live weekly talk-show entitled "Tom Green Live" on AXS TV starting October 3, 2013.[40][41] Green has stated in interviews that the set was modeled after The Late Late Show with Tom Snyder. The show was similar to his web show where there is a featured guest and a long format one-hour discussion. Additionally, fans can call in from Skype. Scheduled guests have included Richard Belzer, Howie Mandel, and Tony Hawk. Season 2 debuted on January 9, 2014 and the finale was April 3, 2014. The show renewed with season 3 debuting on June 12, 2014 and concluded its run with AXS TV on November 20, 2014.

On numerous interviews, Green has stated that he started doing stand-up comedy at the age of 15 but stopped after he started his public-access television show.[42] Green said that going back to stand-up comedy was something he always wanted to do.[42]

In September 2009, Green performed several stand-up comedy shows in Los Angeles, and later appeared at a MySpace secret stand-up event in New York. On November 10, 2009, he announced his first ever world stand-up comedy tour[43] and as of January 2010, has been touring the world going to countries such as Canada, the United States, England, Scotland, and Australia.[44]

Green at the Houston Improv in 2010

The format of Green's act is traditional stand-up comedy which in 2010 has included rap performances. He voices his thoughts on social media, technology, his career in show business, oppression, and social political commentary on society. He often takes time to meet with people in the audience afterwards.

In October 2010, he performed in Belleville, Ontario at the Empire Theatre with his parents and brother in attendance. Green dressed in a Belleville Bulls Jersey donated by a local movie studio he had visited earlier that day. He discussed the city's recent ordeal involving the sentencing of disgraced CFB Trenton Base Commander Russell Williams, stating that he hoped Williams "was having an awesome weekend".[citation needed]

On August 13, 2010, after being invited, Green performed stand-up comedy at the Gathering of the Juggalos. He was later involved in attempting to calm the audience down after Tila Tequila had rocks, excrement and urine thrown at her during her performance at the same event.[45] In subsequent interviews, Green said he successfully calmed the audience down for ten minutes, but things got worse when he left the stage. Tequila continued performing for an additional twenty minutes and eventually suffered facial injuries after being struck in the face by a rock.[45]

In an April 2013 interview on discussing his theories on his stand-up comedy, Green states:

“

"I don’t really like picking on the little guy. I don’t like picking on people who are minorities, less fortunate, disabled or people who are not powerful people. I want to sort of speak truth to power, to government, to the system that we’re living in that we’re not really in control of. I stay away from making fun of people. I don’t do a lot of racial issues. I don’t do a lot of religious humor. I don’t really do a lot of making fun of people for the way they look. I don’t really do a lot of making fun of people for their sexual orientation or their sex. That’s not my style. That’s, by the way, what a lot of people do in comedy. They talk about these things because it’s sometimes an easier laugh. I’m more trying to challenge myself and talk about things like corporate America or addiction to technology or legalizing drugs and the government and freedoms that we have that are being stripped away. It’s finding humor in all of that stuff.

I do feel like I’m trying to change the way people think about their own lives with my standup. I’m not just trying to get a laugh from people, but I actually want people to walk out of there and critically analyze how we’re living our lives in this modern era. We’re stuck on our Facebook pages and giving up our privacy in a surveillance society and we’re forced to go through metal detectors and X-ray machines everywhere we go and giving up our freedoms and living in a fear-based society afraid of terrorism and war and all this stuff. There are a lot of outrageous things that are happening right now in our world that have never happened in my lifetime. I see it happening and it scares me and worries me, so I think if I can get people to laugh about it and think about it and talk about it after the show, I get a lot of enjoyment and fulfillment out of that.[46]

”

Green's September 2011 stand-up performance in Boston aired on Showtime in August 2012;[47] titled "Tom Green Live", it was released on iTunes, on Netflix and on DVD in March 2013.[48] Green performed on The Tonight Show with Jay Leno on August 17, 2012.[48]

Tom Green was married to actress Drew Barrymore from July 7, 2001, to October 15, 2002.[16][19] In December 2001, Green filed for divorce.[19] In 2010, Green has stated that he has not seen Barrymore since the divorce.[49]

In March 2006, Green broke two ribs in Costa Rica when a large wave swept him off of an outcrop where he had been fishing and onto rocks below.[50]

As a 2009 contestant on the reality television game show, The Celebrity Apprentice, Green played to benefit the Butch Walts and Donald Skinner Urologic Cancer Research Foundation. He later stated that he would not be alive today had it not been for Donald G. Skinner, M.D.